Interrupted N-Heterocyclic Carbene-Catalyzed Radical Coupling Strategy: A Versatile Platform for Alkylation and Arylation of [60]Fullerene.

An interrupted N-heterocyclic carbene-catalyzed radical coupling strategy is disclosed for efficient alkylation and arylation of [60]fullerene. This novel and general strategy bridges the gap between organocatalytic radical cross-coupling and functionalization of fullerenes. Readily available feedstocks, remarkably broad substrate scope and functional group compatibility, and convenient late-stage nanomodification of complex molecules make this strategy with incomparable diversity and practicality in the synthesis of monoalkylated and -arylated fullerenes.

Catalytic System-Controlled Regioselective 1,2- and 1,4-Carboannulations of [60]Fullerene.

Selective functionalization of fullerenes is an important but challenging topic in fullerene chemistry and synthetic chemistry. Here we present the first example of catalytic system-controlled regioselective 1,2- and 1,4-addition reactions for the flexible and efficient synthesis of novel 1,2- and 1,4-carbocycle-fused fullerenes via a palladium-catalyzed decarboxylative carboannulation process.